shrinkwrap doesn't go all around a Cylinder
Two questions..


(top row) You're using the wrong projection method in your Shrinkwrap modifier for this case.You have 'Project', along Y of the object space of your array (which is the same as the Y of your original element). Better to use 'Target Normal Project' (along the normals of the target) or 'Closest Surface Point'.
(bottom row) How to get an outward tilt of the peaks? The Shrinkwrap can be modulated by Vertex Weight. Assign a vertex group to the mesh, and weight it with lower values at the peaks. They will be influenced less, if you aim the  Shrinkwrap at the group.